


Don’t Fuck (With) Gangsters

by ElricsFanfics



Category: Homestuck
Genre: 1920s, Alternate Universe - 1920s, Alternate Universe - America, Alternate Universe - Gangsters, Alternate Universe - Historical, Alternate Universe - Human, Alternate Universe - Police, Alternate Universe - Prohibition Era, Caliginous Romance | Kismesis, Crushes, Drinking, Drunk Roxy Lalonde, F/F, Flappers, Gangs, Gangsters, Humanstuck, Illegal Activities, Implied Sexual Content, Karkat Swearing, M/M, Prohibition, Roaring 20s, Slang, Smoking, Speakeasies, Terezi Pyrope Isn't Blind, Underage Drinking
Language: English
Status: Completed
Published: 2019-05-14
Updated: 2019-05-14
Packaged: 2020-03-04 22:57:11
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,329
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18822472
Author URL: https://archiveofourown.org/users/ElricsFanfics/pseuds/ElricsFanfics
Summary: The Empire, a Chicago-based gang headed by Meenah Peixes, has the Alphas and the 8-Balls, two branches located in Detroit aka bootlegging central.Not everyone is a gangster though, some are just normal people. Some are normal people who don’t think things through and end up doing dumb shit with dangerous people.





	Don’t Fuck (With) Gangsters

**Author's Note:**

> What started out very well thought out ended up not so much.

Karkat couldn’t remember exactly how he had been persuaded into going to a speakeasy, but he was there. He refused drinks on principle, staying as sober as ever. It was sort of expected of one at such an establishment to drink which made every interaction increasingly more awkward as the evening progressed.

As content as possible to be a wallflower the entire night, Karkat tried his best to avoid people and cling to his brother. Kankri would have been old enough to drink had it been legal, but it was almost entirely certain he would refuse irregardless. The Vantas boys weren’t known for their outrageous behaviour. They were godsent, model children to parents, and the dullest folks in all of America to everyone else.

“You decided to come with,” Karkat reminded his brother quietly when the older boy grimaced a flapper dancing nearby.

“Why did you come in the first place?” Kankri replied, turning to his brother. The room was large, but dimly lit. Shadows were cast over the faces of anyone not in the center of the room. That didn’t seem to be an issue, though, as that was the populous area, save for maybe to bar.

“Gamzee had been pestering me to come for awhile now, and I couldn’t stand it any more,” Karkat shrugged easily, “I can’t say I’m enjoying myself that much, but it beats sitting around the house.”

“It all seems a bit immoral, if you ask me.”

“Good thing I didn’t.” Karkat rolled his eyes, “Did you happen to see where Gamzee ran off to?”

Kankri shrugged,

“Probably the bar.”

“Thought so.” Karkat pushed himself away from the wall which he was leaning on and waded through the crowd to the bar. To no one’s surprise, he found Gamzee seated there, glass in hand. What was somewhat surprising, however, was the other boy speaking to him.

“Karkat!” Gamzee exclaimed, throwing his arms out, “Where have you been, bro?”

“You’re the one who abandoned us,” He corrected curtly.

“Did I? Huh, sorry about that! But I’d like you to meet my new friend, Tavros.”

“Nice to meet you,” Karkat nodded politely.

“Same to you,” The boy echoed, mirroring the gesture clumsily.

“I think Kankri and I might head out now,” Karkat informed his friend.

“Awww,” Gamzee pouted, “You guys didn’t even do anything!”

“I told you it’s not our scene,” Karkat sighed.

“Just one drink?” Gamzee pleaded, “I swear you’ll have more fun then!”

“I’ll pass.”

His friend frowned, but didn’t protest,

“I’ll see ya later, Karbro.”

“See ya,” He waved, spying Kankri across the room. Despite the illumination condition, his older brother was easy to spot since he never left the house without his signature red vest. Sure, it could be a bit tacky, but his good friend Porrim, a local seamstress has crafted it for him.

“Shit, sorry!” Karkat apologized, realizing he had stepped on someone’s shoe on his journey through the mass of bodies. To his surprise, the owner was a tall man–no boy, likely his age, clad in a tasteful suit and unnecessary sunglasses.

“That’s no dancing getup,” Karkat snorted.

“Not everyone is here to dance,” An even taller man in matching attire responded. He too wore sunglasses, the only difference being that they possessed pointed edges, creating a bold cateye look. Karkat would have normally been inclined to mock the pair, but their height and overall demeanour left him feeling very intimidated.

“C’mon, bro,” the taller one grumbled, nodding toward a booth at the back of the room.

“You ready to–is that booze?” Karkat interrupted himself mid-sentence, looking at his brother in awe.

Kankri held a glass unsurely, swirling around its contents as he stared at it. He looked up,

“Yeah… I got it from a guy back there.” He pointed with his free hand to a man with a cigarette in his mouth and slicked back hair who seemed to be engaged in conversation with the two brothers.

“You’re not gonna drink it, are you?” Karkat wondered out loud.

“I don’t know… it’s quite kind of him, considering how expensive everything is…”

“Do you wanna talk to him?”

“Couldn’t hurt, right?”

“I don’t know, Kankri, I just had a run-in with those two blond guys and I don’t think they’re here just to drink…” Karkat lowered his voice, “Dad would kill us if we got involved with the mob.”

“I know! But the least I could do is thank him!”

Karkat snorted,

“You haven’t even drank it.”

Kankri scowled, taking a cautious sip to spite him.

“How is it?”

“Foul,” the older boy replied with a strangled voice as he set it down, “Now let’s go over.”

Karkat rolled his eyes, but trudged over to the booth. Seated around the table were three men and a woman, all dressed in suits. Two were the blond brothers, one was the slicked-hair man, and the woman was lanky with dark hair and thin-rimmed glasses.

“Good evening, gentlemen,” Kankri smiled with a nod.

“What’s up?” The sharp-shaded man asked, gazing up from his drink lazily.

“I just came to thank you,” He turned to the man in question, “For purchasing that drink for me.”

“Nodda problem, chief,” he grinned, “How’d ya like to join us?”

The tall blond shot his companion a glance, though it was unreadable through his shades.

“My brother and I were just about to leave,” Kankri informed.

“Dhat’s a shame, are ya sure I can’t interest ya in joining us? Booze’s on da house when I’m in town.” He smirked, an unlit ciggarette cocked in his lips.

“I-uh.” Kankri wrung his hands, stuttering nervously.

“Just fuck off then!” The woman snapped, fist hitting the table. She turned to the other black-haired man, “I swear, Cronus, if you hit on one more person while you’re in our city, I’ll bump you off myself!”

“Relax, doll.” Cronus rolled his eyes, “Vriska here gets wound a liddle tight when she hasn’t drank in awhile. Bootlegging really is da business to be in!”

“I’m flattered by your offer,” Kankri mumbled, words finally forming in his throat, “But-“

“Ya brodda can stay too, ya know. What’re you two’s names?”

The Vantas brothers exchanged nervous glances.

“I’m Karkat and he’s Kankri,” the younger spoke.

“Well then, c’mon, Kankri.” Cronus smiled grabbing his hand and pulling him into the booth. Karkat awkwardly sat next to him.

“Drinks for dhese two!” The man shouted to a waitress.

“Right away, Mr. Ampora.” She nodded, scurrying off.

“So,” Cronus’ devilish smirk had yet to fade, “Whaddaya boys up to tonight? Dhis doesn’t really seem like ya scene.”

“It’s not,” Karkat piped up, “My friend dragged us here.”

“Cronus,” The taller blond cleared his throat, “Business first, please?”

The dark-haired man sighed,

“Don’t be such a wet blanket, Dirk! Business can wait! Not like ya brother cares.”

“You know Dave’s here to get used to it,” Dirk answered. His voice was calm, but his teeth seemed partially gritted.

“Can you boys just make up your goddamn minds?” Vriska growled, clenching her fist.

“I mean no offence,” Kankri began gently, “but I don’t think you have much say here, ma’am.”

“Fuck off, kid. I don’t have time to deal with this shit from anyone else.”

“We’re all sort of da big cheeses up here.” Cronus nudged Kankri, “Ya lucky ta be sittin’ with dee Cronus Ampora, let alone gettin’ free drinks from ‘im.”

The waitress returned to their table, a tray in hand with two glasses. Silently, she set one down in front of each Vantas boy.

“Allow me to properly introduce us,” Dirk spoke as the woman retreated, his annoyance had faded, leaving a bit of exasperation in its place.

“I’m Dirk Strider, you may have heard of me? I’m top dog of the Alphas. This is my brother, Dave,” He motioned toward the the boy next to him. The shared the same bright blond hair, but the styles varied. He jerked his head to his side, 

“Vriska Serket, head of the 8-Balls.” Dirk pointed across the table to Cronus, “Cronus Ampora, second-in-command of The Empire.”

“I’m here ‘cus Meenah’s so busy in Chicago at da moment.” He leaned his head against Kankri’s, “I thought folks back home were hotsy-totsy, damn, I shoulda came ta Detroit foreva ‘go!”

A light blush dusted Kankri’s cheeks, but Cronus kept speaking, now to Vriska,

“So, Vrisk, ya still playin’ cat and mouse with dhat cop?”

The woman looked up from her drink, which she had been stirring idly,

“That’s none of your business.”

“You can tell me, doll, I ain’t gonna spill,” Cronus dropped his voice mockingly, leaning forward in the table.

“Oh, fuck off, Cronus,” Vriska snorted, crossing her arms and sitting back, “What I do in my spare time is a private affair.”

“Spare time? So hate-fucking a cop is a hobby a yours now?”

Though she was looking away, one of Vriska’s eyebrows still twitched irritably.

“She is,” Dirk mouthed to the now snickering man who raised an eyebrow interestedly.

Meanwhile, Karkat and Dave had been staring at each other. It seemed to be out of a mutual boredom with the situation. Dave had pushed his shades down to the top of his nose for the sake of fairness, but Karkat knew himself to be very good at staring matches.

Karkat’s eyes, heavy with dark circles from frequent bouts of insomnia, were dry, but he wouldn’t concede to the stranger. He’d gone on for longer before.

Dave, on the other hand, was squinting to ignore the twitch in his eyelids. He slid his drink closer and fumbled for the straw with tongue. His competitor bit his lip, stifling a laugh.

“Shit!” Dave exclaimed, as the glass tipped and spilled a clear liquid across the table.

“Goddammit, Dave!” Dirk sighed, signalling the waitress over. She frantically mopped up the beverage, avoiding eye contact with everyone.

Dave mumbled an apology as she disappeared behind the bar. With the adults conversing again, his gaze met Karkat’s once more.

The shorter boy was covering his mouth with his hand, restraining laughter and mockery. Dave scowled playfully in return, pushing his shades back up upon realizing how they were perched.

Karkat’s eyes darted around the room, attention caught by various flashes of light and snippets of drunken flirting. Though he was with his brother, he was still uneasy to be around gangsters. Dave seemed different though, and put him at ease. Regardless, Kankri was an idiot for staying this long.

He grabbed his brother’s hand, tugging at it gently. Kankri, however, didn’t notice, too caught up blushing at whatever remark Cronus had just made.

Dave cocked his head, picking up on the other boy’s anxiety. He turned to his brother, 

“Imma go outside for a fag. It’s so hot in here.”

Dirk nodded, only half-listening,

“Don’t take all day.”

Dave responded with an affirmation and as he stood up beckoned Karkat to follow.

The blond held the door open for the shorter boy as they exited on the side.

“There’s no reason you couldn’t have smoked inside,” Karkat informed him.

“I know that, but I had to get out of their; it’s always so loud and annoying.”

“I can’t say I don’t agree.”

Dave shoved his hands in his pockets, leaning against the brick of the building,

“I envy you. Even if you do have some family legacy to uphold, it’s gotta be better than mine.”

“Perhaps.”

“There’s zero reason to be nervous around me,” Dave glanced over, “I’m not nearly as important as my bro.”

“That’s good to hear, I guess. Weren’t you here to smoke?”

Dave shrugged,

“Bro says I should, says it’s good for ya, calms ya down. If I’m being honest, I think it stinks. I’d rather get caught bootlegging than take up smoking.”

Karkat stood on the wall next to him. They stated at the sky in silence for a few seconds before,

“Did your brother serve?”

“Huh?”

“Did Dirk serve? In the Great War, that is.”

“Barely. In ‘18 he went overseas, he was only 18. He fought for two months, nearly got decapitated, then came home. The scar on his neck is pretty wicked, but he really doesn’t like people pointing it out. Why do you ask?”

“Smoking settles the nerves, Kankri would probably be the same was if he had fought.”

“Why didn’t he?”

“Church stuff, he volunteered with various charity events raising funds and whatnot.”

“He’s one of the lucky ones.”

“I guess you’re right, Dave.”

“I almost fought.”

“How old are you?” Karkat looked at him, interest piqued.

“16, 13 at the time.”

“Then why?”

“Bro suggested I become a pilot. Said I’d be good at it plus they got all the amenities of actual food and lodging.”

“What stopped you? I know of many who lied about their ages.”

“I convinced him to give me another week to think on it… then he came home with 50 stitches in his neck…”

“I’m sorry…” Karkat whispered, “For prying.”

“Nah, it’s fine. Still better than listening to Cronus hit on your brother.” He smirked, “That one’s easily flustered, isn’t he?”

“Yeah...” Karkat trailed off with a nervous giggle.

“Who’s this broad?” Dave asked, head snapping away to squint at a figure approaching them, “Didn’t think anyone came down this alley.”

“Oh shit…” Karkat muttered.

“Karkat!” A female shouted, “What are you doing here?”

“Hey, Terezi. I’m just visiting a friend.”

A woman came into view, red cateye shades she was wearing illuminated by the moonlight. She stopped in front of Karkat, her nose twitched,

“You reek of cigarettes and alcohol, what’s going on?!” She demanded, grabbing his collar.

“Terezi listen–”

“Whoa, lady! Hands off of him!” Dave growled stepping forward.

“Terezi Pyrope, DPD,” She snapped, flashing a glistening gold badge from her pocket, “Back off, fella.”

“Explain yourself Karkat, I know this isn’t you.”

“I–”

“Leave him alone. I know you’re just on the prowl for speakeasies. Come with me and I’ll show you where it is.”

Terezi released Karkat, turning to Dave,

“Show me.”

The blond gestured over his shoulder, “Lemme take you inside, though. You obviously aren’t enough to handle this whole joint.”

The woman gritted her teeth,

“Fine, but if anything fishy happens, I’m warning you: I’m packing heat.”

Meanwhile, Cronus was gripping Kankri’s thigh under the table as he told Dirk and Vriska of Meenah’s latest affairs in Chicago.

“Shut up for moment is that– Fuck.”

“What’s wrong, Vrisk? Ya see a ghost?”

“It’s damn close enough,” She replied through clenched teeth, “Terezi’s here. And she’s with your brother, Dirk.”

“Terezi? What’s wrong with her?” Kankri asked, looking between her and Vriska, “She’s just a friend of Karkat’s.”

“That bitch has been tryna nail me for a couple months now.”

Cronus winked.

“Don’t get me fucking started with you,” She hissed, not even casting him a sideways glance.

“Keep your cool, Vriska. I can handle this,” Dirk responded calmly, “And Cronus.”

“Yeah?”

“Keep your mouth shut.”

The man frowned, but didn’t speak.

“Hey, lil’ dude, what gives?” Dirk asked as Dave approached their booth, “Who’s this? I told you no chicks on school nights.”

“This is–”

“I’m Terezi Pyrope,” She interrupted, sitting across from him and folding her hands on the table. She kept her voice low, but spoke sternly,

“Dave here has informed me–and I can see for myself–that this place is illegally selling liquor. Would you kindly direct me to the owner of this establishment?”

“You’re sitting right across from them, missy.”

“Great. Now, you can either calmly come with me down to the station, or I will return tomorrow night with a full squad.”

“I’m not the one I'm talking about, Pyrope.”

“Hey, ‘Rezi.” Vriska smirked, leaning forward on the table, “Long time no see, babe.”

“Serket,” She growled through gritted teeth.

“I’d love to stay and chat,” Vriska cooed, donning a fedora, “But I think I’ve had enough fun tonight.”

Dirk stood up, allowing Vriska to exit the booth. Terezi quickly rose to her feet as a response.

“Don’t you fucking leave, Serket. You have a lot to explain.”

“You know I don’t have a goddamn thing to explain,” She stated, back turned to the cop.

Terezi clenched her fists, watching as Vriska sauntered out of the building,

“You can’t escape me, Serket! I know Jane Crocker– best gumshoe in the Midwest!”

Dirk cleared his throat, sitting down again,

“I trust that I’ll see you around?” He chuckled, taking a long sip from his glass.

“So it seems,” She grumbled, walking away.

When Dirk glanced back across the table, he found Dave and Karkat sitting side-by-side, chatting quietly. Cronus and Kankri, however, were missing.

“Lil’ man.” Dave looked up.

“Where’s Cronus at?”

Dave shrugged,

“Not sure where he went, but he left during Vriska’s spat with the cop-gal.”

Dirk grunted, turning toward the rest of the club,

“This night didn’t go as planned. Prepare to head out soon.”

“Okay, bro.”

“Dirk~” A woman cooed from the dancefloor, “Didn't think I’d see you here tonight~”

Dirk sighed standing up and approaching her,

“Hi, Roxy.”

She put her hands on his shoulders, body swaying to the music.

“I’m surprised you’ve never been caught.”

“Maybe I have, babe, maybe I’m just really fucking good at hiding hangovers.”

The man snorted,

“I highly doubt that.”

“Ya’d be surprised,” She grinned, eyes half shut,

“I love to dance…” She trailed off whimsically.

“You’d be a shitty flapper if you didn’t.”

Roxy stuck out her tongue, scowling at him,

“I’m a beautiful flapper and ya know it! Don’t blame me for ya lack of taste.”

“That’s not what I mean, and besides, you’re just not my type– flappers aren’t my type.”

Roxy let go of him, stumbling to get her balance,

“Jake ain’t here tonight, but I’ve been dying to see ya!”

“You saw me just last week.”

“Yeah, but ya never come to this side a town!” She exclaimed.

“Business calls, Rox.”

“Ya always say that,” The woman whined. She looked around,

“Where’s all ya friends? Ya never go out alone.”

“They’ve disbanded. Tonight has been lousy with unexpected interruptions.”

“Am I an unexpecteded interruption?”

“Yes, but I like you.”

“I gotta go. We can talk another time, when you’re not smoked.”

Roxy groaned something unintelligible, drifting away to dance with another man.

“Dave,” Dirk beckoned his brother over, retrieving a cigarette from his pocket, “Let’s go.” Dave nodded at the man.

“Sorry,” He whispered to Karkat, “See ya ‘round?”

The other boy smiled,

“I’m not leaving Detroit any time soon.”

The blond returned the smile half-heartedly, 

“Let’s hope I’m not as well.”

“Here.” Karkat handed him a slip of paper.

“What’s this?”

“Business card, I work at my father’s bank.”

“I’ll try to remember to give you a call.”

“I know you won’t forget, dumbass.”

Dave snorted, pushing up his shades. He pocketed the card and stood up.

“Hurry up!” Dirk grunted.

Dave waved farewell to Karkat and walked behind his brother who had impatiently begun to leave already.

“Kankri!” Karkat exclaimed, noticing his brother’s return to the booth, “What the actual fuck? Where were you?!”

Kankri’s face was flushed completely red as he murmured into his hand.

“Answer me. You can’t just fuck off randomly, especially if it was with that random gangster!”

“He took me to the bathroom…”

“Huh?”

“He said he some pretty… lavacious stuff earlier…”

“You are going to be the shittiest priest ever if you let people in your pants that easily.”

“Shut up…” Kankri moaned.

“Where’d that fucker go anyway?”

“Cronus? I’m not sure…”

“Bet he doesn’t even have the decency to let you finish,” Karkat added under his breath, scanning the room for him.

“It’s fine… let’s just go home.”

“You okay?” Karkat asked his brother seriously, trying to look him in the eye.

“Feeling a lot of different emotions right now,” Kankri admitted. He wiped sweat from his brow and met his brother’s gaze, “Is masturbation trigger warning-worthy?”

**Author's Note:**

> Ahhh I couldn’t help myself! Shoving characters into 20s roles was so fun!!


End file.
